14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid

Base Information

• Chemical Name: 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid
• CAS No.: 197508-62-6
• Molecular Formula: C20H32O3
• Molecular Weight: 320.472
• DSSTox Substance ID: DTXSID001267714
• Wikidata: Q27115853
• Metabolomics Workbench ID: 2760
• ChEMBL ID: CHEMBL269319
• Mol file: 197508-62-6.mol

Synonyms:14,15-EET;14,15-epoxy-5,8,11-eicosatrienoic acid;14,15-epoxy-5,8,11-eicosatrienoic acid, (2alpha(5Z,8Z,11Z),3alpha)-isomer;14,15-epoxyeicosatrienoic acid;14,15-oxido-5,8,11-eicosatrienoic acid

Chemical Property of 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid

Chemical Property:

• PSA: 49.83000
• LogP: 5.42790
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 396

Purity/Quality:

99% ^*data from raw suppliers

14,15-EpoxyeicosatrienoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC1C(O1)CC=CCC=CCC=CCCCC(=O)O
• Isomeric SMILES: CCCCCC1C(O1)C/C=C\C/C=C\C/C=C\CCCC(=O)O

Technology Process of 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid

There total 18 articles about 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → cis-14,15-epoxyeicosatrienoic acid (197508-62-6,81276-03-1)

Guidance literature:

With human recombinant cytochrome P₄₅₀ 2E₁; stereoselective reaction; Enzymatic reaction;

DOI:10.1194/jlr.M003061

Reference yield: 93.0%

docosahexaenoic acid (6217-54-5) → (±)-16,17-epoxy-4Z,7Z,10Z,13Z,19Z-docosapentaenoic acid (895127-63-6) + cis-14,15-epoxyeicosatrienoic acid (197508-62-6,81276-03-1)

Guidance literature:

With human recombinant cytochrome P₄₅₀ 2E₁; stereoselective reaction; Enzymatic reaction;

DOI:10.1194/jlr.M003061

Reference yield: 56.0%

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 8,9-epoxyeicosa-5(Z),11(Z),14(Z)-trienoic acid (184488-44-6,81246-85-7) + cis-14,15-epoxyeicosatrienoic acid (197508-62-6,81276-03-1) + 11,12-cis-epoxyeicosatrienoic acid (200960-01-6,81276-02-0,87173-81-7)

Guidance literature:

With human recombinant cytochrome P₄₅₀ 2C₉; stereoselective reaction; Enzymatic reaction;

DOI:10.1194/jlr.M003061

upstream raw materials:

Peroxyarachidonsaeure

arachidonic acid imidazolide

all cis 5,8,11,14-eicosatetraenoic acid

eicosa-cis-5,8,11-trans-14-tetraenoic acid

Downstream raw materials:

14,15-DHET

15-HPETE

C₂₆H₃₈N₂O₄S

14,15-Epoxyeicosatrienoic acid methylester

Refernces

• 1、 Deng, Bing-Qing,Luo, Ying,Kang, Xin,Li, Chang-Bin,Morisseau, Christophe,Yang, Jun,Lee, Kin Sing Stephen,Huang, Jian,Hu, Da-Yong,Wu, Ming-Yu,Peng, Ai,Hammock, Bruce D.,Liu, Jun-Yan. "Epoxide metabolites of arachidonate and docosahexaenoate function conversely in acute kidney injury involved in GSK3β signaling". . p. 12608 - 12613. Retrieved 2017.
• 2、 Xie, Xiang-Qun,Yang, Hongqin,Choi, Greg,Lin, Sunyuan,Makriyannis, Alexandros. "Synthesis of 15N and 13C selectively labeled anandamide". . p. 775 - 784. Retrieved 2002.
• 3、 El-Sherbeni, Ahmed A.,El-Kadi, Ayman O. S.. "Repurposing Resveratrol and Fluconazole to Modulate Human Cytochrome P450-Mediated Arachidonic Acid Metabolism". . p. 1278 - 1288. Retrieved 2016/04/26.